1-(4-Iodocubyl)-2-phenylacetylene | 134971-19-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(4-Iodocubyl)-2-phenylacetylene
• 英文别名: 1-Iodo-4-(2-phenylethynyl)cubane
• CAS: 134971-19-0
• 化学式: C₁₆H₁₁I
• 分子量: 330.168
• InChiKey: YWLLWFUTIDIFMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  4-Iodocubyl Methyl Ketone 在 copper(I) bromide 、 四(三苯基膦)钯 三乙胺 作用下， 生成 1-(4-Iodocubyl)-2-phenylacetylene
  参考文献：
  名称：

  Synthesis of alkynylcyclooctatetraenes and alkynylcubanes

  摘要：

  The couplings of a variety of iodocubanes with terminal acetylenes in refluxing NEt3 in the presence of Cu(I) and Pd(0) were examined. The products, isolated in about 50% yield, were not alkynylcubanes but were instead the first examples of alkynyl-1,3,5,7-cyclooctatetraenes. The first examples of alkynylcubanes (cubylacetylenes) were themselves synthesized in modest yield by Negishi's procedure from alkyl cubyl ketones. Cubylacetylenes were shown to be stable under Heck-like coupling conditions and potentially useful thereby for the introduction of the cubylacetylene moiety into complex systems.

  DOI：

  10.1021/jo00017a028

文献信息

• Cubane Cross-Coupling and Cubane-Porphyrin Arrays
  作者：Stefan S. R. Bernhard、Gemma M. Locke、Shane Plunkett、Alina Meindl、Keith J. Flanagan、Mathias O. Senge

  DOI：10.1002/chem.201704344

  日期：2018.1.24

  Herein, an improved methodology for aryl‐cubane cross‐coupling is reported. The peculiarities of the cubane core and its behavior during cross‐coupling conditions were analyzed, while the versatility of this adapted Baran cross‐coupling methodology was demonstrated by the synthesis of various aryl‐cubane systems, including coupling products of cubanes and porphyrins. Furthermore, arm extension of alkynyl‐cubanes

  本文报道了一种改进的芳基-古巴交叉偶联方法。分析了古巴核的特殊性及其在交叉耦合条件下的行为，同时通过各种芳基-古巴体系的合成，包括古巴和卟啉的偶联产物，证明了这种适应性的Baran交叉耦合方法的多功能性。此外，还展示了Sonogashira反应对炔基-古巴酮的臂延伸，这显示了在钯催化剂存在下，古巴尼核心的稳定性的第一个证据。